HCID 131721085, compound → HCID 131721084, compound

Participants

Reaction Steps

2.0 g (0.011 mol) of ethyl rac-2-oxotricyclo[2.2.1.03,5 ]heptane-7-carboxylate (compound of the formula I where R1 =Et) are stirred in 25 ml of 0.1M potassium phosphate buffer, pH=7, at 50° C. with 300 mg of lipase SP 526 from Candida antarctica (Novo Nordisk) using a magnetic stirrer. The pH is kept constant with the aid of an autotitrator. After metering in approximately 12.0 ml of 0.5M NaOH, the reaction mixture is extracted with tert-butyl methyl ether. After drying with Na2SO4 and concentrating the organic phase, 0.89 g (0.005 mol, 90%) of ethyl (1R,7R)-(+)-2-oxotricyclo[2.2.1.03,5 ]heptane-7-carboxylate (HPLC [Chiracel OD, n-hexane+EtOH:100+1.1 ml/min, 210 nm]; 98% ee) is obtained.

Provenance & Evidence